Potassium Carbonate → HCID 22148820, compound

HRID 1370498Notes

Reaction equation

HRID 1370498 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:13][C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([OH:21])=[C:16]([Cl:22])[CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Cl:20][C:18]1[CH:19]=[C:14]([NH2:13])[CH:15]=[C:16]([Cl:22])[C:17]=1[O:21][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 800374-Amino-2,6-dichlorophenolHCID 2731322-Chloro-6-methoxybenzothiazole

Product 1

HCID 22148820HCID 22148820, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-chloro-6-methoxybenzothiazole (prepared as described by Weinstock et.al., J.Med.Chem.30: p1166 (1987)) and 4-Amino-2,6-dichlorophenol 1.3 g (available from Tokyo Chemical Industry Co., Ltd.) in DMSO(9 mL), was added K2CO3 3.12 g. The mixture was heated at 150° C. for 3 h. The reaction mixture was purified by column chromatography(silica gel, AcOEt:hexane=1:2) to provide the aniline 105 (1.43 g, 56%). mp 158-160° C.

Workup

  1. customThe reaction mixture was purified by column chromatography(silica gel, AcOEt:hexane=1:2)

Sources & evidence

ORD record
ord-b780f690f2884af3b49b9307ab5ffd6a
Source dataset
uspto-grants-2003_06
Patent number
US06583157B2

Reaction notes

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